


Day Twenty-Six: Roleplay

by TobytheWise



Series: 2018 Kinktober [26]
Category: Supernatural
Genre: Alpha Dean, Crossdressing, Dirty Talk, Feminization, Knotting, M/M, Omega Castiel, Panties, Rimming, Roleplay, Teacher Dean Winchester
Language: English
Status: Completed
Published: 2018-10-26
Updated: 2018-10-26
Packaged: 2019-08-06 23:20:43
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 974
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16397027
Author URL: https://archiveofourown.org/users/TobytheWise/pseuds/TobytheWise
Summary: “Mr. Winchester? Can I please speak with you?” Castiel asks in his most innocent voice which makes Dean’s cock harden in his jeans. Fuck, his husband is hot.“Of course,” Dean says as he nods towards the chair he has for when Cas comes and works with him in his office. “Have a seat.”Cas sits, crossing his legs in a way that gives Dean a brief view of the lacy, black panties he’s wearing under that skirt. “I’m so sorry I didn’t turn in my last assignment, Mr. Winchester.”Dean takes his glasses off, cleaning them with the bottom of his shirt. “It is a shame. That assignment was worth 50 perfect of your grade. Without it you’re sure to fail.”





	Day Twenty-Six: Roleplay

Dean finishes up the last of his grading. He sets his glasses down in order to rub his face and his eyes. When he puts them back on his husband is standing in front of him, wearing a slutty schoolgirl outfit. Dean swallows his surprise as he takes in his sexy as fuck husband who’s kicking his heeled feet, looking innocently as Dean.

“Mr. Winchester? Can I please speak with you?” Castiel asks in his most innocent voice which makes Dean’s cock harden in his jeans. Fuck, his husband is hot. 

“Of course,” Dean says as he nods towards the chair he has for when Cas comes and works with him in his office. “Have a seat.”

Cas sits, crossing his legs in a way that gives Dean a brief view of the lacy, black panties he’s wearing under that skirt. “I’m so sorry I didn’t turn in my last assignment, Mr. Winchester.”

Dean takes his glasses off, cleaning them with the bottom of his shirt. “It is a shame. That assignment was worth 50 perfect of your grade. Without it you’re sure to fail.”

Cas gives him his best pout. “But Mr. Winchester, I’ve been so good throughout your class.” Then his face morphs like he just got an idea. “Isn’t there anything at all I could do to bring my grade back up. I really need to pass.”

Dean places his glasses back on his face. He looks Cas up and down. “What do you have in mind?”

Cas smiles. “I have an idea or two, Mr. Winchester.”

Dean’s breath picks up at Cas’ flirty tone. His cock is so hard against his zipper. “Show me,” he breathes. 

Cas stands immediately, his skirt whooshing in a way that gives Dean a whiff of Cas’ sweet slick. Cas kneels between Dean’s open knees, running his hands up Dean’s thighs. Cas buries his nose in Dean’s crotch, rubbing his cheek up and down Dean’s hard cock. 

“Such a dirty girl,” Dean whispers, eyes never leaving Cas’ face. 

“Only for you, Mr. Winchester.” Cas opens Dean’s jeans and takes his cock out, licking it up and down before sucking the head into his mouth. 

“Fuck,” Dean moans as Cas takes his cock into his throat, swallowing around the head. “So good, baby.”

Cas’ hands reach up and begin to tweak Dean’s nipples and the alpha already feels his ball tightening. He pulls Cas’ hair until the omega pops off his cock. “You want my load in your mouth or your ass?”

Cas scrambles up off the ground. “My ass, please,” he says before pulling the back of his skirt up and laying his chest against Dean’s desk. 

“Fuck,” Dean curses at the display. Cas’ perfect, round ass cheeks on display as that black thong runs along his crack. “So pretty,” Dean marvels as he gets himself naked. 

He runs his hands up and down Cas’ cheeks until the omega is tilting his hips back and whimpering. Dean drops to his knees, slapping Cas’ cheek hard. “Such a dirty little slut, aren’t you? Coming in here and seducing a married man.”

Cas moans long and low as Dean flicks his tongue through Cas’ crease, licking up as much slick as he can. The taste explodes against his tongue and causes a rumble of pleasure to vibrate through Dean’s chest. He laps over Cas’ hole until his lips and chin are covered in his omega’s juices. 

“Please,” Cas whimpers, one of his hands tangles in Dean’s hair, pulling the alpha’s face tighter against his ass. 

“Such a greedy slut,” Dean says, nipping one of Cas’ ass cheeks. 

“Please. Want you in my greedy ass! I need it so fucking bad, Mr. Winchester.”

“Need my to fill this pretty pussy, baby?”

Dean stands up as Cas lets out the prettiest whimper. “Yes. Please fill my pussy.”

Dean runs his cock through Cas’ slick, teasing his omega’s hole until Cas’ legs shake with anticipation. The head of his cock catched on Cas’ hole causing the omega to gasp. Dean lays his chest against Cas’ back, holding the omega down against the desk, trapping him there. 

“Please,” Cas whispers desperately and finally Dean pushes forward, sheathing his entire length inside Cas’ ass in one thrust. 

“Such a perfect pussy for me. Milk the cum from my balls with that cunt and I’ll be sure to let you pass your class, baby.”

Cas’ head nods before he places his forehead down on the table. He squeezes his ass perfectly and Dean’s has to grit his teeth so he doesn’t come straight away.

“Please,” Cas groans. Sweat begins to cause his bangs to stick to his forehead, his cheeks are flushed deliciously. 

“Such a perfect omega with a perfect hole.”

“Your hole. All yours.”

Dean’s hands grip Cas’ hips tight. “You’re damn right,” Dean growls, his thrusts picking up as the sound of their skin slapping together rings loud in Dean’s office. “Mine!”

Cas cries out as Dean bites down on the back of his neck. His ass clamps down on Dean’s cock and Dean is lost in the pleasure. His knot pops, locking him inside Cas’ ass as he coats Cas’ insides with his warm cum. 

Dean wraps his arms around Cas as he sits down in his chair, pulling Cas into his lap so they can wait together for his knot to go down. Dean nuzzles the back of Cas’ neck as the omega sighs contently. 

“That was so sexy, Dean. I’m definitely keeping this outfit.” 

Dean gives Cas a nip before chuckling. “Agreed. This was the perfect way to relax after all that grading.” He squeezes Cas tight. “Thank you. I love you, baby.”

Cas tilts his head to the side so he can kiss Dean. “Love you too, Mr. Winchester.”

“I think you’ve earned that A, Mr. Winchester.”


End file.
